Steroid nuclei containing nitrogen have been shown to possess a wide range of physiological activities. The vast majority of these azasteroids are derived by modification of naturally occurring steroids.
Of the known azasteroids (3,2-c)-2'-phenylpyrazole of 9.alpha.-fluoro-6,16.alpha.-dimethyl-.DELTA..sup.6 -hydrocortisone is claimed to be he most potent anti-inflammatory steroid known--over 2000 times as powerful as hydrocortisone itself. The 0-methyl ether of 16-azaestrone has exhibited significant hypocholesterolemic activity but possesses less than 1.01% of the estrogenic activity of the parent estrone. 4-Dimethylaminoethyl-4-aza-5-cholesten-3-one methiodide has been shown to irreversibly inhibit the growth of Bacillus subtilis cultures at concentrations as low as 1 .mu.g/ml. 17-Hydroxy-17 .alpha.-methylandrostano[3,2]-.mu. pyrazole exhibits an antiovulatory activity one-fifth of that observed for norethisterone when administered orally in rats.
Monoazasteroids were first synthesized in the 1930's as a "synthetic decarboxylase." Some of the known azasteroids are derivatives of 4,4-dimethyl-5-.alpha.androst-14-ene and are intermediates in steroid-terpene structure correlations. It is apparent that the 15,16-diazasteroids, and especially the 15-monoazasteroids have been little studied, despite the fact that this latter class of compounds combines the steroid nucleus with the often biologically active indole nucleus in a single structure.